


Dress for the job you want

by Animeguera



Category: Supernatural
Genre: Alternate Universe- No Supernatural, Bisexual Dean Winchester, M/M, Mechanic Dean, Minor Lisa Braeden/Dean Winchester, Professor Castiel, Slow Build
Language: English
Status: In-Progress
Published: 2017-12-27
Updated: 2018-03-23
Packaged: 2019-02-22 08:40:59
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 12
Words: 13,815
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13163319
Author URL: https://archiveofourown.org/users/Animeguera/pseuds/Animeguera
Summary: “Movie teacher.” Dean’s mouth replied faster than his brain could interpret. To his credit, Castiel tried to hide his confusion. His jaw opened without consent again. “At the local college, I teach about movies.” Dean said, holding his breath. That was a blatant lie and a terrible lie.~~~~~Six months after that disastrous first date.Updates Every other Friday





	1. So it begins

Dean is a liar. He had practice telling his father that both Sammy and him had enough to eat, knowing Sammy had eaten most of the food while his father was gone. He remembers teasing Rhonda Hurley about having tightest ass he’s ever laid eyes on. Rhonda rolled eyes at him. Dean remembers telling Sammy that he was fine daily for three years, even though the nightmares never stopped and the voice inside his head telling him he wasn’t good enough never truly died. Dean remembers adding five inches to the fish he caught everytime he found an outdoorsy girl that found that amazing. He lied constantly if he was honest with himself. He was an accidently follower of Barney Stinson’s Bro Code. Lying to women so he could have sex with him was practically his default. His lies to men were unpracticed and sloppy, due to lack of experience.

  
He had walked over to the man with good intentions, honest good intentions to ask him out on a proper date. Dean hadn’t had one in a while. He tried simple words, no lines. “What are you studying?”

  
He was sure it those blue eyes that captivated him. That strong jaw that confused his better judgement. That graveyard rough voice that spoke of theology and memorized bible verses, even a few passages of the Quran. That voice lulled him in and made him feel inadequate, so when that dark voice ask him what he did for a living, Dean could barely voice an answer. He choked on his whiskey, coughed and muttered ‘mechanic’ quickly. The man leaned in closer, touching his jaw to Dean’s mouth, unaware of the existence of other people’s personal space and quietly ask him to repeated himself.

  
“Movie teacher.” Dean’s mouth replied faster than his brain could interpret. To his credit, Castiel tried to hide his confusion. His jaw opened without consent again. “At the local college, I teach about movies.” Dean said, holding his breath. That was a blatant lie and a terrible lie.

  
It wasn’t as impressive as being a theology phd candidate at the university in Lawrence, Dean knew that. He just knew, that voice told him, that being a mechanic would make him not good enough to even talk to Castiel. He hated when that voice mocked him loudly. It was always louder when he hit on guys. He overrode that voice when he heard that rough laugh. It warmed his gut.That’s what he deserves for attempting to pick up a guy at Sammy’s University. He wasn’t sure what the event was even for anymore.

  
Castiel gave him a strange look, like he was considering whether he was telling the truth. Dean prayed to the closest thing to a God he admitted to that Castiel wouldn’t doubt his profession. His extremely made up, ridiculous, worse than a bro-code profession. “That sounds intriguing, do you teach about a specific genre?”

  
“Horror movies.” Dean breathed out. Horror movies were simple right? Monster chases girl, virgin girl lives, monster gets caught, the end. At the word horror, Castiel lit up. “I thoroughly enjoy the sixty era of movies.” He smiled. Dean blanked out at the smile, he felt warmth again, pride. “The nuclear fear caused some interesting notions of monsters.” Dean nodded, both hearing Castiel’s words and not fully comprehending them. He dropped his voice again, Dean leaned in to listen carefully. “There’s a series of classic horror films starting next month.” Dean nodded, it was going to be Halloween season soon. Dean looked at Castiel, Castiel was looking over his shoulder his eyebrows furrowed. Dean finally let air into his lungs.

  
Before he had a chance to say another word, Castiel muttered low, “Excuse me,” walking away, leaving Dean struggling to breath, reminding himself he has to breathe. He had been drowning in a sea of blue. Dean went to find his giant of a brother. He wasn’t hard to spot, even in a throng of people. Not many could match his height, his head stuck out a group of older people. Two men with graying hair and an older sleight woman, two feet shorter than Sam.

  
Sipping his drink, Dean came up to the group, introducing himself. Sam’s professors were discussing the next set of exams his brother would have to endure.Dean laughed, knowing those days of studying were behind him. He grasped a promise from each of them that Sam would have an extra hard test. Sam glared at Dean, while the professors had a great laugh.

  
“Dean, I want you to meet Professor Novak. He’s teaching my theology philosophy class.” Sam introduced as he pulled in a man with dark brown hair.  
“What kind of class is that? Do you philosophize what God thinks about?” Sam sighed.

  
A rough newly familiar voice answered. “To reconcile and prove the existence of God with philosophy.” He smirked at Dean. “Or disprove.”  
Dean’s voice caught in his breath, again. He choked out a response finally. “Good luck with that.” Castiel’s deep laugh caught the group by surprise, they gawked at him.

  
“That’s the first time I’ve heard you laugh, Professor.” He just shrugged and stared at Dean hesitantly. The conversation continued as Dean stole glances at the professor who never laughed, wondering if he was going to bring up his lie to this group of people. Sam knew he was just a mechanic. The dark grease smudges under his fingernails were an obvious sign, despite how hard he scrubbed at them. Slowly, the conversation lost his interest and focus. His thoughts wandered to how worthless his job was. He wasn’t a professor, he didn’t have any formal education, he was nothing.

  
He should’ve let the train of thought stop. He knew the symptoms. His breathing slowed. His thoughts continued to swirl, negatively. His throat dried up. His drink was empty and he wished for some water. He excused himself as best as he could. He needed to stop thinking, he needed to stop his thoughts. He walked quickly to a corner and pulled out the paperback he kept hidden in his coat pocket. His eyes blurred but he forced himself to focus on the words. Slowly the thoughts ebbed away as words filled his mind. Dean turned the page and kept reading. The crowd fell away, the noise dropped and slowly, slowly the voice he hated dropped away as he focused on the words. Stay focused on the words.

  
He barely remembered having to leave as Dean read the entire book in one sitting. Sammy pulled him away as the night ended and he drove both of them home. He said nothing and let Dean read his book. Even if he had asked how Dean how he was, Dean would have lied and said he was fine.


	2. Date Night

**Summary for the Chapter:**

> Steam escapes the cup as the pink lips blow into the steam. Dean holds his breath, remembering those round lips around his own anatomy.

Today’s lie of the day: He’s not tired. He possibly offered to take his date out for coffee instead of a catching a drink tonight so he could stay awake during their date. It’s a tad awkward to date someone after you’ve already slept with them but she seemed interested in continuing whatever they were doing into the next week. Dean suppresses a yawn and cover his mouth with his hand. He drops an extra dollar into the tip jar as he picks up their coffees and sashays his way over to the too small table in the corner.

He smiles as the beautiful brunette blushes up at him. “Thanks.” She mutters, taking the hot coffee and taking off the lid. Steam escapes the cup as the pink lips blow into the steam. Dean holds his breath, remembering those round lips around his own anatomy. He moves to sit down quickly, adjusting himself. Anything Lisa did reminded him of sex, it was exciting and exhausting. He bit down on another yawn as he took a sip of his own coffee, letting the burn wake him up more.

He had met Lisa at a bar a weekend ago and they had seen each other non stop since. That first weekend was filled with late night coupling and early morning groping. Lisa was a yoga instructor and she showed Dean just how far she could bend her body. Downward dog was his favorite position so far. He grinned at her, just as she took a drink of her own now tepid drink. He realized he had nothing to say to her. Lisa mentioned she was off on Wednesday night.  
Dean took his cue. “How about a movie? They’re playing a bunch of black and white films down on Fourth. Charlie Chaplin, Nosferatu...”

“Nosferatu? I’ve never heard of it.”

Here, Dean could shine. “It’s the original vampire film, way before Dracula. Its black and white and awesome.”

She shrugged, “I’m more into Charlie Chaplin.” Dean smiled, forgetting his earlier tiredness. “Let’s go Wednesday night. It’s been a while since I’ve had movie popcorn.” Dean agrees, finishing his coffee.

**~~~~**

  
Dean is prepared. He’s dressed in his best pair of jeans and an actual button down shirt, buttons undone. He attempted to clean the grease from his hands and it just made them dry and cracked. He picked up his phone quickly as soon as it rang. Lisa’s name on the screen told him all he needed to know. He answered anyways. With a few words Lisa made some very scandalous promises for the weekend as she explained that her kid had a fever.

“Take care of the kid, I hope he feels better soon.” Lisa apologizes and hangs up, leaving Dean alone at the theater. Even if he still wanted to watch the movie, he’s never enjoyed sitting in a theater by himself. He walks outside into the cooler air, letting the candescent lights wash over him as he thinks about texting his brother. A grumbling voice makes him look up.

“That’s not polite.” Castiel’s voice tore through the noise of grumbling teenagers he was surrounded with. “Apologize.” The command in his voice makes Dean swallow tightly. He watches as the brunette in his still too long trench coat, surrounded by five sullen teenagers, takes control of their small group towards the ticket line. He utterly forgot how handsome the professor looked, even clean shaven.

“Hey, Cas.” Dean utters softly. His voice doesn’t carry over the growing crowd. Dean pushes past the small teenager who looks much too young. “Cas!” Dean states loudly, grabbing the man’s attention. Castiel turns, his eyes tight and boring into Dean’s head.

“Yes?” Dean’s heart falls, how could he be so caustic at him. “Dean?” Dean nods, happy that the professor remembers his name. Since he was able to make him laugh, he should be memorable at the very least. Castiel smiles at him and Dean gets lost in those blue eyes once more. He concludes Castiel has very dark powers, considering he is now sitting in a dark theater, surrounded by ungrateful complaining teenagers. He barely recalls agreeing to this. He was just being a nice guy and greeting his brother’s professor after being stood up for a very legitimate reason. His plan has gone incredibly sideways.

Castiel mutters a few words and Dean stares at him. He’s still waiting for the explanation of why Castiel is in charge of the LGBQT teens for a school night showing a horror film that he knows none of the children have ever heard of. The movie is just as he remembers and Dean gets lost in the films so he forget where he is. He barely recalls he was supposed to be watching Charlie Chaplin with Lisa.

He doesn’t remember having a club like that when he was in school. Even if there was, he doubts he would’ve joined. His small family never stayed in one town for much longer than a few months. He doubts it would have mattered, but he has a glimmer of hope that it might’ve helped with his darkness.

As they exit, the teenagers are talking excitedly about the film and he joins them. He forgets the preposterous lie he told Castiel the night they met and wishes he had chosen a more believable lie. Like the one he told Lisa, that he owned the auto shop he worked at. Everyone can root for an entrepreneur. “I would like to ask you to speak at our next meeting about the cultural significance of the film, if you could.” Castiel asks, not two inches away from Dean’s face, staring him down.

Dean stutters a “Whaat?” Castiel looks confused at Dean for a second before explaining.

“The club sponsor is inviting to share some of your horror film theory as a point of discussion next week.” Movie teacher! Dean remembers the stupid profession in that instant. Nodding his head in remembrance. “I’ll ask Sam for your number and text you the details.” Castiel wrangles the five teenages easily and orders his next words. “Please thank Mr. Winchester.”

The teenager mutter a few thanks as they walk towards the back of the theater where he presumes their vehicles are parked. Dean stands alone in the bright lights of the theater as movie goers exit the building, wondering why he tells lies.


	3. Planning

**Summary for the Chapter:**

> “Dean, no.” Are his first words before looking up. “I have to study tonight. I can’t help you be on the prowl.”

The first thing he does is drive home to talk to Sam. Sam has been the one who talked up the redhead at the bar about Dean rescuing a cat after it had fallen from a tree. Dean is allergic to cats, making it more absurd. Sam has been the jerk making a busty brunette feel awkward and let Dean be the savior, pushing himself between Sam and her. He saved the brunette and she expressed that gratitude on her knees. Dean has even been the one to start a fight, just so Sam could impress a girl by pulling her away from it to protect her. He needs some backup. 

Dean finds him in the apartment, hunched over in the kitchen table, surrounded by books. The television is playing in the background. Sam never liked the place to be too quiet, it reminds him of the calm before the storm of their father. 

Dean pulls the book from in front of Sam’s face and looks at it. The author is C. Novak. “Samm-my,” he sings. 

“Dean, no.” Are his first words before looking up. “I have to study tonight. I can’t help you be on the prowl.” He reaches for book and takes down a note. 

“I have never said the word prowl.” Dean counters, grabbing a beer from the fridge. 

“What do you want? Don’t you have a date with Lisa?” Sam says as he highlights in his book. Dean cringes, now they won’t be able to sell them back at the end of the year. 

He shrugs. “Her kid was sick. I need help with something else.”  
  
He sips at his drink until Sam sighs. “With what?”

“Your professor is gonna ask for my number and I want you to give it to him.” How soon would he ask for his number from Sam? How close are they really?

“Dean, no! You cannot date one of my professors.” Sam finally looks away from his books to glare at his brother. 

“That’s not what it’s about.” Dean says pushing away from the counter. “Just listen, I might’ve told him I’m someone else and now he needs me to do something. Just don’t mention I’m a mechanic and give him my cell.” 

Sam is quiet again as he checks his laptop that's off to the side.  “He just emailed me. Why not tell him no?” Sam asks as he readily types back a response including Dean’s cell phone number. 

He doesn’t say that he wishes he was that person. He wishes he was more than just a mechanic. He wishes he could be as smart as him. He does the only thing he knows how to do when he’s caught in a corner. “It’s a challenge, you know how much I love those.” He lies. 

“Whatever, jerk.”

“Bitch.” Sam returns to his book, Dean leaves the small kitchen to let Sam continue with his studies. Sam’s decision to stay in town was more for Dean’s benefit than his own. Dean did convince him that two years here, studying and working would be worth if he could save enough to go to Stanford as a Junior. School was cheaper and Dean could help him save some money on rent and other things. Dean was happy he could keep his brother near him for at least one more year. Even in this cramped, dingy one bedroom apartment. Dean pulls a blanket over him as he lays on the couch, his bed. He pulls out his own laptop, two years older and Sam’s old school laptop. 

He types out a few searches into the browser and starts getting acquainted with the cultural significance of Nosferatu. He falls asleep, with the glow of his laptop as he reads about the lawsuit Stroker’s wife brought against the studio. It’s the first time since Dean dropped out of high school that he’s studied for anything. 

**Notes for the Chapter:**

> Short chapter! Stay tuned next week for when Dean speaks to Castiel's club of teenagers
> 
> 1/5/2018


	4. Presentation

**Summary for the Chapter:**

> Dean goes to present to Castiel's LGBQT club.

 

Dean has only been out of high school for eight years. He hadn’t graduated, opting to take the GED exam at fifteen and going straight to work. Most people wouldn’t hire an emancipated minor but Bobby did. If he strains his brain, he could opt to remember the feeling of emptiness he felt those first few years as he worked sixty hour weeks to keep Sam in school. High school seems frivolous in comparison to those days and he envies the young teenages as they walk around free of burdens. 

The LGBQT club that Castiel sponsored met during lunch. Bobby had let him take an extra long lunch break without an explanation. He hadn’t asked for so much as a day off that hadn’t related to Sam in years. For a few minutes, Dean was worried. He was worried that he couldn’t do this. He couldn’t pretend to be an educator that he made up. He counted his breaths. He had to exude confidence he knew that. People didn’t care about facts or truth, if you looked confident about what you said, people believed it. That’s the only way he had survived Sam’s high school years. He projected confidence that he was the adult in the family, that Dean Winchester had all his shit together and wasn’t the scared little boy his father made him to be. 

Dean double checked the room number in his phone as he was led into the hallway. There was a smatter of conversations happening around him and he drowned out the noise. `The game was on. He even dressed in slacks and a button down shirt. He took off his over jacket. He left on his ill fitting suit jacket and walk confidently into the classroom. His breath stopped as he found Professor Novak, Castiel, bending across a desk to reach something on the side. He was dressed in a similar suit as him, dark black, not faded and the pants were tight on his backside. Dean bit his lip to keep from whistling in appreciation. Sam’s teacher looked even better from behind. 

With his attention fully focused, he missed seeing the teenagers snicker as they sat in their tiny little desks. Dean didn’t like those desks, they were too small for him. Sam must’ve hated them even more after he got this third growth spurt in high school. “Mr. Novak!” A girl squealed so loudly that Dean squeezed his eyes at the shrillness. The professor turned quickly, knocking down more books from the desk. He muttered an apology as he bent down again to pick them up, exposing his backside once more. The teenagers snickered again as Dean tried to keep a passive look on his face and held his jacket in front of his crotch. Think of Sammy in drag.....Sammy in drag. 

“Mr. Winchester, I’m pleased you made an appearance.” Professor Novak said, his voice deep and seductive. That might’ve been wishful thinking on Dean’s part because his voice faltered on his response. 

“Yes.” He said. 

“I-We,” he corrected, ”eagerly await your presentation.” Dean gulped, presenting confidence and a grinning smile. Dean had this covered. He could bullshit with the best of them.

“Too short of time for a presentation, this will be more of a conversation.” He uttered and then turned his back to the professor. He saw a smattering of young teenagers staring at him without much interest. “Who here has read Bram Stoker’s Dracula?” He started. 

His conversation was mostly with two of the teenagers who engaged with him the most. Dean glanced at Castiel as he sat behind him in the desk, that most likely didn’t belong to him. His blue eyes watched him closely and Dean enjoyed the feeling. They talked the finer points of the movie and even encouraged the teenages to pull out their phones and google Spongebob Squarepants and Nosferatu. The teenagers laughed at the stupid joke that probably didn’t make sense to them years ago. He talked about the lawsuit that Stoker’s wife won and almost destroyed the move from existence. 

A young girl with short blonde hair had actually read Dracula. She wore black pants, black shirt and studded leather bracelet. She guessed that Nosferatu actually started the lore that vampires can be destroyed by sunlight, since it didn’t happen in the novel. She grinned at him and then put back the scowl that she had before. Dean enjoyed talking so much about the movie and other vampire movies that he didn’t realize he had used up all his time. Castiel interrupted him softly to tell him that lunchtime was ending. Everyone had to head back to class soon. Some of the teenagers actually whined at that. Dean was hoping because movies were more interesting that actual classwork and he was engaging enough.

“That was well done. You actually connected with them.” Castiel’s expression was in gratitude. 

“Uh, thanks I guess, man.” Dean shrugged, holding his neck and looking at the floor. 

“You are a surprisingly excellent orator.” Castiel complimented as he gathered his notes from the desk. Dean didn’t quite understand the compliment. 

“Are you hitting on me?” Dean asked, he wouldn’t have minded, it just wasn’t the normal way men hit on him. Men usually called him pretty and went straight to ask for sexual favors.                                                                 

Castiel looked embarrassed and coughed. “No, that was not a flirtation. I simply wanted to relay how well you connected with our lost youth here.” He smirked at the small joke. Dean laughed, remember how they got to talking about the  _ The Lost Boys _ . Dean smiled again and watched how Castiel’s stuttered. “Thank you.” Castiel’s color was flushing a bit and that encouraged Dean even more. 

“So, how did a prof like you end up with the lost youth?” Dean dropped his head and peered at  Castiel closely.

Castiel swallowed holding tightly on his papers. “My niece suggested the club required a more authentic sponsor.” Dean swallowed, hoping for more clarification. He had hoped that it was obvious to Castiel that Dean was hitting on him the first night they had met. After seeing him at the theater, he wasn’t sure. The dude didn’t make a single move on him. He was enticing and adorable. 

Dean moved closer and Castiel froze in place. “Which one are you?” He asked lowering his voice as he stepped into Castiel’s personal space. “I’m the third one.” He uttered quietly, it was easier to not say that particular word out loud. Dean preferred to let his body do the talking for him. Castiel was still staring at him and frozen in place, his face hot with blood. The door opened violently, pulling Dean away from Castiel before he could answer. Students started flooding into the classroom unaware or uncaring of the two grown men in the room. “See ya later, Cas.” Dean said loudly as he started walking towards the door.   
“The second one.” Castiel said as Dean made it to the door. Dean gave his best smile and winked at Castiel as he left the classroom, navigating through the traffic best he could. It was a great feeling to know he had exceeded expectations of a professor. He felt he was also able to knock him off balance. He had made a grown man with more education than he could count blush greatly. It was a great day.

**Notes for the Chapter:**

> Posting schedule will be on Fridays early in the mornings.


	5. Thanksgiving thought

**Summary for the Chapter:**

> In which Castiel ponders about Dean and by magic makes him appear while grocery shopping.

Castiel loathes liars. Dean Winchester is definitely a liar.He knows Winchester is his last name because of his brother Sam. He shouldn’t have given into temptation. He closes his eyes to try and clear his thoughts, but all he sees is those green eyes smiling back at him. Castiel huffs out a breath and increases the pace of his running. Maybe he can distract himself from his thoughts. It’s a ridiculous thought. All he can think of is Dean’s words to him.  _ I’m the third one.  _ It was an awkward flirtation but a very straightforward admission of his sexuality. It was extremely honest and not at all what Castiel was expecting from a man who made up a profession on the spot in an attempt to impress him.

His feet thudded rhythmically on the concrete. He passes the green trees of the park, like he always does on his run. He skirted a woman walking with her child and ran past them. He kept up the brisk pace.  His breath was patterned. The cold brisk air filled his lungs. Still his thoughts were faster than his own feet.  He had been weak and wanted to embarrass the man, to catch him in the outrageous lie he had concocted and deigned to tell Castiel. Liars like Dean took advantage of those around him. Dean had thought Castiel was easily taken advantage of, he wanted to prove him wrong. 

Asking Dean to talk to his LGBQT club was spontaneous. His mischievous plan didn’t work out as he had intended. Castiel had underestimated how easily a handsome man could get him so flustered. Instead of Dean cancelling or floundering to speak about a vampire film, Dean met his challenge and flourished. Dean spoke easily to the young teenagers, he had engaged them in conversation that not many people can easily do. Castiel was impressed, since he still had difficult capturing his student’s attention in a class they chose to take. It made him realize that Dean was much more than he presented. 

Castiel was then shocked by Dean’s advance on him. Despite his anger, it brought a warmth. He still remembered those green eyes twinkling, smiling and desiring him.  Halfway through his run, Castiel’s thoughts finally turned back to being productive. He had planned out the next week of his classes, the topics for his students to discuss and how to prepare them for the winter final. He was cold from the sweat and his breath was shortened. He knew he had ran too hard for his normal daily run. He slowed to a walk and stopped to stretch. His thoughts finally calm despite those green eyes that haunted him. He still had his number, but Castiel would never use it again. Castiel was stronger than that.

 

~~~~

 

Castiel was in agony in the grocery store. He had stopped in the frozen meats aisle and stared at the bin of frozen turkeys. People flitted around him, grabbing a turkey and placing it in their carts without hesitation. Castiel stayed frozen, looking at the turkeys. He knew his reaction was not the norm. He knew he could just walk away and grab a frozen pizza like he usually does, he could grab two frozen pizzas and a pie just to eat in excess in name of the holiday. 

Normally, Castiel would have skipped this section of the grocery store. Today, he is mesmerized and stuck in place staring a frozen turkeys, of all things. Thanksgiving became a weird holiday in the Novak household, by some unspoken rule, no one really celebrated it anymore. Castiel doesn’t have issues with the holiday itself but a frozen turkey seems intimidating. He’s seen a frozen bird used as deadly weapon. 

“Professor?” A voice startles him out of his memories, Castiel looks up and continues to gaze upward to Sam Winchester’s face. He attempts a smile to ease his student. It must fail spectacularly because Sam looks even more worried. 

“Hello, Sam.” He decides to move a bit away from the turkeys so he can make an exit before he gets captivated again. He feels the chill of the frozen meat section as he steps back again, colliding with a very warm and solid body.

“Woah, professor.” Dean’s voice fills his ears and he sighs in defeat. Of course, this is how Castiel’s day would proceed today. He deserves it really for letting Dean monopolize his thoughts so much during his run. Despite being completely on balance, he feels Dean’s hands on his shoulders steadying him. Dean has very strong hands, that grip him tightly and he has other ideas of where those hands could be used. Dean Winchester keeps leading him into temptation....willingly he might add. 

“Apologies.” Dean is still behind Castiel, his body flush against him. Sam is towering above him, studying him. He then makes a very rude gesture, at Dean he assumes, as Sam’s eyes have left his face. He jerks his head to the side and Dean’s hands release him instantly. Sam gives him a bright watt smile that feels almost too much. “Excuse me, I must take my leave. ” Castiel says, walking away. His basket empty of any food that he had wanted to purchase when he walked in this grocery store. He hears a  _ Happy Thanksgiving  _ shouted at him, Castiel waves back at them, not wanting to be rude, but unable to return the holiday greeting. He has been embarrassed enough from his interactions with Dean Winchester. 


	6. Late Night Books

**Summary for the Chapter:**

> Sam Winchester likes to buy books when he's drunk. What a nerd!

“Sam Winchester is a nerd!” Dean shouts to the empty campus. He laughs as Sam shoves him to the side. Sam making the best bitch face he can as he laughs along his brother. The college campus echoed back silence, with finals over, the majority of the student body was already off campus celebrating.The laughing was induced by a few extra beers they both consumed at the nearby bar. A bar that didn’t look too closely at identification. Dean was still extremely sober, being the designated driver. He never drinks more than two beers an hour anymore. Not if he wants to keep his bad thoughts at bay. The chill wind blew and woke Dean up. Sam was still laughing as they walked, his entire body shaking. A night out was Dean’s gift to him for finishing his exams for the semester. The inebriated joy on his face was worth it. It had been dollar beer night anyways. 

Sam stood up straight and made a declaration. “Dean! I gotta buy a book.” Slurring his words just a bit.

“Dude, again? Jesus.” Dean muttered as he followed the inebriated giant to the glowing light of the campus bookstore that was still open at 2 in the morning. Sam stood in front of the door, pondering how it worked, so Dean opened the door to let him inside. If he didn’t help him buy the book he thought he needed, Sammy wouldn’t shut up about the entire night. It’s how the Winchesters gathered an eclectic collection of books. Dean didn’t mind really, there were worse things they could spend the little frivolous money they had than on books. Dean always read them anyways once he got bored. He actually enjoyed Cat’s Cradle and continued to read that author, even without Sam’s drunken book shopping.  Dean used to  wallow in self misery when he drank too much. His kid brother buys books, like a nerd. 

Sam was humming loudly, mouthing some words to some song, walking through the aisles, his body dancing along badly. The blonde student working the register barely acknowledged them. She continued to read her textbook and glanced up every so often to make sure they were still in the store. Dean followed Sam around the store, picking up books he dropped and steering when he deviated towards a shelf, all the way to the back of the store. Sam finally found what he was looking for, or at least something that caught his attention. 

Dean’s attention was stolen by the clearance aisle with a non fiction called  _ The Monster Show _ . There were over a dozen copies of several Halloween related books that were marked down to ridiculous prices. It tweaked Dean’s curiosity, especially after the adhoc talk he had made to the high school club months ago. Castiel hadn’t contacted him since, which hadn’t been an issue for Dean. His relationship with Lisa had been going well enough. He saw her every couple of weeks for drinks and sex. Lisa hadn’t wanted to escalate it to something more. Dean was fine with the casual fling, for now. He still worked at least fifty hours a week and he opted work on Saturdays too. He hadn’t thought of Professor Novak in weeks, not since he felt his solid body at the grocery store before Thanksgiving. He still remembers the brightness of his blue eyes. He remembers the flush of his face when Dean stepped into his personal space. 

Dean can’t be a professor like Castiel but a little reading never hurt anyone. He grabbed one of each kind of book that related to horror movies in any way and walked to the register. Sam was already there, proud of his choice. It was a thematic cookbook. He placed his books on the counter. He nodded when the cashier asked if it was all together. 

Sam stared at her as she rung up the purchase. It was unnerving how long he kept his eyes on her. “What’s your name?” He asked, his head in his hand as he leaned on the counter, with his height, he bent at the waist. Some semblance of a pose. Dean rolled his eyes and grabbed Sam’s wallet from his jacket and handed her some bills. 

“Jessica.” She muttered, not bothering to look up from the register as she counted out the money. 

“You’re pretty gorgeous.” Sam responded, his voice sighing. Dean grabbed the bag and felt the need to record this event but couldn’t bring himself to look away from the impending trainwreck.

“You’re pretty drunk.” Jessica answered, glaring at Sam. Dean offered a shrug and small smile of apology and pulled Sam away before he did something more ridiculous like profess his undying love for her. It would not be the first time. Jessica seemed way out of his league. 

Dean finally resigned to help Sam at a chance of getting laid. Dean pulled his brother up to full height and nodded at Jessica. “This is my brother, Sam Winchester, pre-law and he thinks you’re cute. Whatddya say you give him a chance once he’s sober?” 

Jessica looked up at the bleary eyed brother. She eyed Dean as well.  “Give me his number, I have an idea.” Jessica smirked as she pulled out her own phone. 

“Is it going to be embarrassing for him?” 

“Hell yes.” He rattled off Sammy’s number and was grinning the whole time. “You’re a terrible brother.” Jessica mused as she saved the contact information. 

“I just got him a cute blonde’s phone number!” Jessica laughed and waved him away, returning to her textbook. Dean chucked the bag of books to Sammy’s hands as he pulled his brother towards the door. 

 

**~~~~**

 

The next morning, Sam was hungover and miserable. Dean was getting ready for work as his brother groaned at his coffee and breakfast. “Don’t let me do that again.” Dean packed his sandwich and pulled his backpack up on his shoulder. It was also one of Sammy’s hand me ups. 

“Not until you pass next semester’s exams.” Dean responded. He came back to the kitchen and slammed his hand on the table next to Sam. Sam jumped up in surprise and groaned at the pain. 

“Jerk.” He muttered hiding his head in his arms. 

“Bitch.” Dean laughed as he left the apartment. He had left Sammy’s cookbook in the bag from the book store. The rest of the books, he had stuffed in Sam’s old backpack while Sammy feigned interest in the eggs Dean had cooked him. He just wanted to read them in peace. He had never explained to Sam what thing his professor had asked him to do. He wanted to keep this secret to himself. He didn’t have to share everything with Sam. 

 


	7. Tempting

**Summary for the Chapter:**

> Castiel and Dean happen to meet at the park, Castiel is overjoyed but Dean receives some bad news.

Castiel runs straight into temptation. He can’t be faulted, he thinks, he was full of adrenaline and endorphins from him run and he just happens upon Sam’s older attractive brother. Dean is just sitting in the bench in the park where he takes his weekend runs. It’s almost fate and Castiel laughs at the notion. He’s too much of a coward to walk away and he’s too excited to stop himself from running towards Dean. 

Dean’s gaze is focused at this waist and he barely glances up towards Castiel’s face  as Castiel brakes hard in front of him. “Hello, Dean.” Dean finally looks to Castiel’s face, his face a bit confused as he squeaks out a greeting. He wasn’t sure how to initiate flirtation, so Castiel attempts to move the conversation forward with the only thing they had in common, Sam. “Sam did well on his exam.” Dean nodded in agreement. Castiel waited and Dean still contributed no words to this barest excuse of a conversation. 

Perhaps Castiel was mistaken in Dean’s interest in him. Dean finally spoke. “You should have made it harder.” Castiel smiled at Dean’s response. It could have been a double entendre and a vague attempt at flirting. Castiel made his leave then, having nothing else to talk about with a man who lied about what he did for a living. He had exhausted his one commonality and he should finish his run before his body cooled down. 

Castiel continued his run and he watched a beautiful brunette woman sat down with Dean at the bench. Castiel lost his breath but continued on. Perhaps Dean had lied about more than just his profession, perhaps he had lied about his availability as well.  

~~~~

Dean has met many young kids in his life. He knew how to talk to kids. Sam had always been younger than him. Sammy was also smarter than him, so talking to Sammy had been like talking to someone his age or older. When the auto shop had a few younger children running around because the parent was talking with Bobby, Dean always kneeled down and talk to them about the car he just finished working on. The little smiles and laughter he pulled out of them was worth the bite in his knees.  He wished he worked with children sometimes. He remembered the prof’s teenager club and smiled in recollection. 

This kid, Ben, might be one of the coolest kids he’s ever going to meet. Ben likes AC/DC, wears a leather jacket, just like Dean. He tries to remember if he met Lisa earlier in his youth and made this kid with her. She had told him at least twice that no, he wasn’t the father of her super amazing kid. He’d have been eighteen years old at that time. Which was a particularly slutty time of his, but only on the weekends.       

He hadn’t officially met the kid of course. It was mid-December, but Dean did buy the kid a Christmas present. It was just a couple of DVDs that he picked up from the bargain earlier in the week. Lisa hadn’t had any expectations but he still enjoyed gift giving during the holidays, especially when he could afford it. He was waiting at the park, Lisa was going to bring her son to meet Dean. It had been two months since their first hookup. Dean was anxious and ready to meet the kid. He was happy to meet him. 

He kept looking around, enjoying the fresh air, despite the cold breeze. He saw a few joggers run around. One jogger was running towards him with purpose. It made Dean tense with anticipation and worry. The jogger had a lean toned body and was wearing very tight shorts that made Dean suck in his breath. His gaze was aiming low, so he didn’t realize the mess of dark hair and the blue eyes staring down at him in amusement. “Hello, Dean.”

Dean looked up and his brain forgot how to process words again. The sweat on Castiel’s face was distracting. He managed a quick, “Hi.” 

His deep voice captured Dean again. “Sam did well on his exam.”  Dean nodded, it was the right thing to do, but he still had nothing to add to the conversation. He watched Castiel’s confused face, his adorable blue eyes shining. Castiel’s broad shoulders and trim waist, he wanted Castiel to walk away so he could see his tight ass that Dean knew he would have. 

“You should have made it harder.” Dean said finally after more than a few seconds of silence than was socially acceptable. Castiel smiled broadly at that.

“Next time, I shall.” Castiel finally did step away and Dean appreciated the view and then chastised himself for having the most idiotic conversation with a man who has hot and had double his own intelligence. He finally saw Lisa walking towards him, he was distracted by the flowing of her brown hair in the cold wind. 

Castiel watched Dean’s gaze focus and her and muttered something. Dean thanked the professor for teaching his brother. He could feel the disappointment radiating from the professor and it made him hope, despite his current relationship with a brunette woman. Lisa looked tiny even in her wool knee length jacket. She was walking alone. Dean glanced around looking for Ben playing around nearby. Castiel jogged away without anymore notice. 

Lisa had no expression in her face as she walked up to Dean. “Where’s Ben?” Dean asked, holding onto the Christmas wrapped present a little too tightly, wrinkling the paper. 

She looked right into Dean’s eyes and spoke softly. “I didn’t think it would be a good idea for him to meet you.” Dean stayed silent. He had been working on his angry outbursts. This was a perfect time to practice. “Since this just a casual thing between us, I don’t want Ben to get attached. I mean, it’s not serious between us.”

That was what made Dean snap. “I am serious about you!” Lisa didn’t flinch at his outburst. She had a pitying look on her face, it made Dean cringe. He knew it had to be good to be true that a beautiful woman with a pre-started family would be interested in just a mechanic like him. Not that she knew he didn’t own the business he worked at. He figured that was a conversation for later.

“I didn’t mean you.” Lisa said, attempting to comfort him by patting his shoulder. She sat down next to him on the bench. Her gloved hands in her lap as she waited for Dean to respond. 

“Really?” Dean sighed, dropping his head in his hands. His world view shifting just a bit. He had thought he was finally growing up. The gift slowly fell to the cold concrete. 

“You are really fun,” Lisa smiled sadly, “I’ve had a lot of fun with you. But I never envisioned this getting serious.” She laughed, pushing hair behind her ear. “I’m actually a little scared of it actually.”

“You don’t even want to try?” Dean asked, looking at Lisa. He sat up straight, not letting this feeling dwell. He couldn’t let this feeling dwell much longer. 

Lisa shrugged. “Ben’s father is getting out on parole. I’m not sure that’s a good idea right now.” She grabbed Dean’s hand. “I have the night off, Ben’s at a friends house.” She casually ran her hand up Dean’s thigh. Dean could barely feel it through his jean and her gloved hand. “Want to have some fun?” She smirked at him. Dean smiled back, Lisa could make him feel enough to make him forget this feeling. 

He still gave Lisa  the gift as she left his apartment later that night. She smiled at him and gave him a kiss and told him thanks. Her eyes were sad as she took the gift. Dean has seen that look before. He’s seen in his own face when he’s made a decision that would affect more than his own life. He only hoped it would be better news for the kid.

~~~~

The next day at work, Dean had kept all his focus on the car he had been assigned. He didn’t stop to think. He didn’t stop to take a lunch. He had come to work as soon as Lisa had left his apartment earlier that morning. He worked until late into the night. Bobby might’ve noticed his mood but said nothing, just asking him to close up the shop when he was done being an idjit. Dean had to keep his attention on fixing the next car in line. He had to keep his body working and his mind from wandering. He couldn’t risk going home or to a bar and drinking himself stupid. As soon as he had a clear minute, he deleted Lisa’s number from his phone. She hadn’t said they were broken up, she hadn’t said those exact words, but that’s exactly what had happened. 

If he let himself think, he would think himself into a bad place. He had been doing so good with keeping away from that place. He didn’t want to go back. He would do anything to avoid ending up there again. So he worked. He woke up on the cold floor of the shop the next morning, a blanket thrown over him. His body was sore and wrecked from sleeping on the floor. It had been a couple of years since had slept in the shop. 

He noticed Bobby standing over him, holding two cups of coffee. He handed one to Dean. “Work as long as you want, son.” Bobby walked away without another word. Dean drank his coffee and thought, well as least he was gonna get a bigger paycheck just in time for Christmas. 


	8. Sam's new friend

**Summary for the Chapter:**

> Sam has a new friend texting him.

Sam was glad for winter break, it gave him a chance to get some extra cash. His exams were over for the year and he did exceptionally well. His future plans required him to have excellent grades and he worked hard to achieve that goal. So much so, he really rarely participated in the social aspects of his college experience. Sam’s part time job and hours studying took up a lot of his time. There had been a party a few weeks ago before exams that he admitted, he drank far too much and had to call his brother to drive him home. His brother hadn’t been disappointed, not that he would. Dean personally made Sam’s fake identification, so if he ever got caught with alcohol, he could at least walk away. He used to enter the bars around campus and he used it sometimes to drink at the Roadhouse with Dean on Trivia nights.

Sam drank for fun, so he wasn’t too worried about making it a habit like his father. John Winchester was a lesson in how not to drink. Dean almost followed that path, but Sam made him stop. Dean didn’t stop drinking, not all the way. Dean limited himself to two beers per hour with plenty of water in between. Dean never drank hard liquor unless it was a celebration or a holiday. He was clocking out after working a graveyard shift as a stocker when Sam’s phone buzzed with a new message.

 

Unknown: _Hey Sam_

 

He didn’t recognize the number, so he texted back immediately asking who it was.

 

Unknown: _You don’t remember me? Way to make a girl feel special._

 

Uh oh. He crossed his fingers internally that it wasn’t a study partner.

 

Sam: Sorry. I must’ve not saved your number.

Unknown: _Name’s Jess, in case you don’t remember that either._

 

Jess? He couldn’t remember ever talking to a Jess. His mind scrambled for a needle of his haystack mind to find where he could’ve met a Jess. The university was large but not so much so. He knew a lot of the people in his classes. After two semesters, the only class he really felt he didn’t know anybody was in Dr. Novak’s class. That had a lot more upperclassmen and Sam almost regrets taking the class.

 

Sam: Were you in Dr. Novak’s class?

Jess: _Took it last semester. Do you remember going to that party last month?_

 

Oh, great. He found a girl at the party and gave her his phone number. He wishes he could remember a girl. He hadn’t been blacking out, he remembers calling Dean and he remembers getting home.

 

Sam: The Greek Giving Smash, it as a great time.

Jess: _We hooked up there, I had a great time too ;)_

 

What....? He would’ve remembered hooking up with a woman. He hoped he had worn protection if he had.

 

Sam: I don’t remember a Jess.

 

Somebody had to be screwing with him.

 

Jess: _:( Awww, we had a lot of fun together._

Sam: I don’t recall that. I wasn’t that drunk that night to forget.

Jess: _I remember you saying you wanted to buy books, Sam._

 

Well, he does tend to do that when he’s drinking. Sometime about the smell of books is enticing when he’s drinking. It makes him feel like he’s not stupid for drinking.

 

Sam: No, I didn’t.

 

Lots of people knew that.  He remembers loudly declaring that a lot at parties. It got a few laughs and occasionally free books.

 

Jess: _Sam, I’m pregnant._

Sam: Congrats?

Jess: _It's yours, dummy._

 

This wasn’t possible, he would’ve used protection. Every time he had been with a girl he had used protection. Even if he had been drinking. He stubbornly checked the two condoms he carried in his wallet. Still there. This had to be a joke. This had to be Dean. Same walked faster. The daylight shining through the clouds. The cold chill waking him up. Dean had to be at home, sending him messages from a burner cell.

 

Sam: What? No, even if we did that, I would’ve used protection.

Jess: _You’re sure the condom didn’t break? Because I’ve only boned you, Sam._

Jess: _Sam?_

 

Even thought he was sure it was Dean, he knew it was within the realm of possibility. If it was true, Dean was going to kill him. They were barely making ends meet as it is. If he knocked up a girl, he’d have to drop out of school. Just the thought was nauseating. Sam panicked. If it was true, he guessed it was the right thing to do. If he was wrong, Dean would be freaking out right now.

  
Sam: Marry me.

 

Sam started running. He barely stopped to check the two messages, he had the apartment in view.

 

Jess: _What?_

Jess: _No, dude._

 

Well, he went all in. No point in being coy about it.

 

Sam: I’ll take care of you and the baby. Seriously, Jess, marry me.

 

~~~~

 

Sam had been out all night on a graveyard shift. Dean didn’t like him working too hard while he had classes. During breaks, it was fair game to work all night. Dean might’ve taken advantage by reading in Sam’s bed and then falling asleep. As soon as he wakes in the morning, he strips the sheets and replaces them with the clean sheets from the closet. Sam slams open the door and yells out. “Dean!” He comes out of Sam’s bedroom innocently, with the dirty sheets in his arms. He tried to act innocent, pulling up his own blanket from the couch.

“What’s up, buttercup?” Dean dropped the soiled sheets into a laundry basket and look at a bewildered yet angry Sam Winchester at full height.

“Stop it with the texts!” Sam slammed his hand down on the table. Dean didn’t have to feign his confusion at those words.

“What texts? I haven’t even seen my phone today.” Dean said, glancing around the room to look for his missing phone. He drags himself back to Sam’s room and finds it thrown on the floor, along with his boxer briefs. As soon he steps out of the room, Sam doesn’t wait for him to explain and grabs his phone, flitting through the apps quickly. “Dude! Privacy?!” He snatches his phone back and stuffs it in his back pocket. “What the hell are you all worked up about?”

Sam’s face falls. “It wasn’t you?” Dean glares at him, demanding a better explanation with his expression. “Oh, God!” Sam’s arms pulled into themselves. He bent at his waist and clutched his stomach and his face looked green.

“Sammy, are you alright? Did you eat some shrooms? I told you that hippie stuff was not good for you.” Dean put his hand on his brother’s shoulder, truly worried he had become sick with something.

“I got a girl pregnant.” Sam said quietly.

That got Dean’s attention. “You got laid?” He questions loudly. “Man, I’m so,” Dean stops halfway, fully comprehending his words, “proud?” He takes a breath. “What? Who? When?” He stops before he utters _how_ because he doesn’t really need to know that.

“I’m going to be sick.” Sam said softly, sitting down at the table. Dean pulled the trash closer to Sam just in case.

“Me too.” He thought for a second. “After I kick your ass!” Dean adds, shoving his brother.

Sam sits stock still for a quarter of an hour as another message comes through his phone. He hands the phone to Dean, his hand shaking.

Dean reads the last message that comes through his brother’s phone.

 

Jess: _Dude, this is a joke. Who the hell proposes through text?_

Jess: _I won’t marry you, but I like you enough to go to dinner, hot stuff._

Dean scrolled through the whole conversation for more context, starting at the top, where the messages had started a few minutes ago.

Dean starts laughing before he could stop himself. It overtakes his whole body, he starts shaking and forgetting to breath. “You..” Laugh. “Asked...” Breath. “Her...” Chuckle. “To Marry...” Taking a deep breath. “You?!” His laughter consumed him again as he fought to laugh and breath. Sam’s face morphed from surprise to embarrassment to anger. A serious bitch erupted in his face as he stared down Dean. He started muttering, “I can’t believe she went through with it.”

Sam was shaking as he tried to find his voice. “You knew about this!”  Dean shook his head.

“I had no idea what she was going to do! She is hilarious, Sam.” Sam frowned in confusion. “I gave her your phone number the night you drunk yourself silly after your exams. You were so wasted when you were hitting on her.” Dean smirked. “I might’ve helped you out.”

“I can’t believe you did that.”

“How else are you supposed to lose your virginity? She was really cute by the way.” Dean grabbed the laundry basket.  “You should take her out.” He was out the door with a roll of quarters and the dirty bed sheets.


	9. Trivia Night

**Summary for the Chapter:**

> Dean's trivia night has him meeting someone from his past, who is connected to his present.
> 
> “Are you courting my sister while already committed in an existing relationship?” Dean had to take a moment to translate Cas’s proper wording into something he could understand.  
> “I was flirting, not courting or whatever!” Dean answered the accusation. Castiel just stared at Dean, his fury rolling off of him. “What’s wrong professor, want me to take you out on a date instead?” Dean deflected the accusation.

Dean really shouldn’t encourage illegal activities. He was doing a favor for his little brother. His very under drinking age old little brother and his new girlfriend. Mostly he knew that it was stupid to create a fake id for a girl he barely met. Even if her joke on Sam was pretty spectacular. It wasn’t as if the bars around the university were really strict on checking identification when most of their clientele were not of age to enjoy the alcoholic beverages. Sam had begged, absolutely begged for Dean to make the identification for her. Sam and his girlfriend were at the stage where he wanted to do everything to impress her. Sam called it a Christmas present for himself and for Jess.

 ~~~~

 

It was that lull of time in between Christmas and the New Year, which meant that their favorite bar was packed with people who needed somewhere to take their family from out of town. It was good business for Ellen and Jo. Sam picked up a couple of shifts during the lunch hours. Dean grabbed a few shifts in the evening after working in the garage. It wasn’t much but it didn’t help pay for a few nice things for the start of the year. Sam needed new books after all and new shoes. The kid still hadn’t stopped growing into that lanky body of his.

Tonight, neither of the Winchesters were working. Tonight, they sat in a table, rather than a booth closer to the bar. The yellow dimmed lights painting the room in a soft glow. The wooden floor of the Roadhouse looked dirty but that was only because it was well worn. The booths needed some work but the bar was always presentable. And tonight, Jo, Ellen’s blonde daughter, held a microphone in her hand and a knife her boot. Just to keep the more aggressive of patrons from getting too rowdy. The last scummer who grabbed Jo’s ass was flipped on his back and had a knife to his ribs in two seconds. She smiled as she threatened to puncture a hole in his lungs. That guy never came back, but it was a lesson to everyone in view.

Jess was along for the ride and Sam counted it as a date. Dean didn’t mind, considering he met the girl before Sam did. He approved honestly, she had a great sense of humor. Plus, they needed the additional brain for trivia. Ellen was left to bartend alone as another temporary employee waited tables. Dean arrived late, letting Jess and Sam have dinner alone to start as a proper date. Sam had a beer waiting for him when he joined their table. Jess smirked at him, her way of saying hello.

Dean had never learned much in school. He always bullshitted his way through any test he had to take. So, he was surprised when Sam had invited him to Trivia night at a nearby bar by his campus. It had started as a one off thing, until it turned into a Thursday night tradition for the Winchesters.

“Uranus!” Dean shouted as quick as he could. Sam started laughing, he was well into his fifth beer of the night. He didn’t have classes during winter break and a guaranteed designated driver in Dean. Jess was faring better than her new beau. Dean sat back down in his seat and drank his glass of water, his first beer bottle of the hour sitting empty in front of him.

Dean tried to pay attention to the next question but he was distracted by the flick of red hair at a nearby table. He hadn’t seen this beauty walk in, he would have taken notice. He was glad she was not brunette. He caught her hazel eyes staring at him and he smirked at her. She smiled back shyly. Sitting at her table were two other guys, Dean prayed they were family and not a boyfriend.

He missed the next question, but he saw the redhead get up from the table and stroll to the bar, eyeing Dean the entire path there. She put her elbows on the bar and leaned forward, her backside on showcase for Dean. He wasn’t complaining. There was a only a few minutes in between each question and Team Winter Break already lost the points for this question. It was a perfect moment to go grab more beers and get that girl’s attention.

Dean grabs the empty bottles from their table, carries them to the bar, Ellen takes them quickly and sets down three beers. Dean nods and Ellen rolls her eyes as he drops a twenty on the counter. He turns to the redhead beside and smiles. He thinks she might look familiar but takes a chance. “Can I buy you a drink?”

The redhead looks shocked then shakes her head. She pulls away from the bar and returns to her table. It was a strange interaction, but Dean shrugs, perhaps she was intimidated by his gorgeous face. Dean takes his beers, he gets back to the table with Sam and Jess just as the next question is asked. The redhead is forgotten as Dean focuses on remembering his sports trivia on baseball.

Trivia ends with Dean, Sam and Jess poorer than when the night began. It was close, them taking second place. “I wish Bobby would still come to Trivia night, he always knows the history questions.” Sam laments.

“I guess that education isn’t helping you much then, Sammy.”  Dean sighed, taking a drink of his glass of water finishing it quickly.

“Shut up, jerk.” Sam looked down to Jess, she patted his head and drank more from her beer.

“Who’s Bobby?” Jess asks.

“He’s this grumpy old man who took us in when Sammy was a kid.” Dean answered.

“How sweet. Why did he stop?”

“Bobby decided he’d rather go to bed early than hang out with his favorite employee.” Dean replied. “Bobby runs an autoshop. Sammy used to work there, until he was too good to fix cars for a living.” Dean answered honestly. Sam glared at him but smiled perhaps still under the influence. “I still help Bobby out.” Dean admitted smiling,

“I didn’t know you could fix cars, Sam.”

“Yea,” Sam said, grabbing Jess’s hand. “Dean taught me everything I know.” Jess’s eyes shone with admiration. “Ready to head out?”

Dean shook his head. “You kids go, I’m gonna cast my net around here.” Sam frowned.

“I’ll make sure Sam gets home safely.” Jess promised, leading her tall date out the door.

“Get a ride if you need one! Wrap it up!” Dean yells loudly. Making several patrons turn to stare at him. Ellen glares at him from the bar and Jo puts her hand on her hips. He shrugs at them, it was solid advice for anyone in the restaurant bar. He grabs the trash from the table again and migrates to the bar. Ellen stares him down as she puts the bottles into the recycling bin behind the bar. “What?” She raises her eyebrow in question. Dean sighs. It had been almost a full month since his break up with Lisa. He wasn’t sure why everyone was still worried. Ellen glances up at the clock and looks at Dean. He nods and Ellen puts down a fresh beer bottle on the bar in front of him. Her face said “don’t fall off the wagon,” like Dean was actually an alcoholic. He wasn’t. He was close, but he stepped away from the cliff.

Dean took the bottle and pretended to sip it, wanting it to last longer. He took a turn around the room with his eyes. It was late enough that most of the families that came for dinner had already left. The patrons left were at the bar with Dean or finishing up their drinks at the tables. Jo took up the bussing duties and started clearing and cleaning tables. A man next to him was fairly handsome face, but he was staring at the blonde next to him. Dean moved on, to the two girls that were chatting at the end of the bar. Another redhead and a brunette. He moved to stand up, just as the redhead kissed the brunette. Dean knew he had lost already.

The bar hadn’t given him any good options. Resigned, he took a long drink from his beer. He spotted the red hair again at the table with the two men. The redhead who ran out on him at the bar earlier glanced at him again and smiled. A big smile that was a little unnerving. Dean didn’t wanted to continue that, so he asked for a glass of water. He almost finished the whole glass, when a new person sat on the left of him.

It was the smiling redhead, Dean smiled and nodded at her. “I remember you now, Dean.” Uh, oh. Dean continued to smile, glancing at the door, hoping to make a quick exit. “I can’t believe it.” She started laughing. Dean frowned now. He had taken a few redheads to bed and quickly flitted through the names.

“Anna?” She didn’t stop laughing, but nodded in acceptance.

“Are you still a mechanic? I remember you were good with your hands.” An honest grin came to Dean’s face. He remembered Anna.

“Yea, totally.” He answered. Anna twirled her hair, looking at Dean with intrigue.

“Dean?” A deep voice interrupted their awkward reunion. He recognized that voice.

Dean turned around to face the voice and found, “Castiel?” He wasn’t wearing his trenchcoat. He was in slacks still, a button down blue shirt and jacket, but no tie. Beside Castiel stood a shorter man with light brown hair down to his ears. He had a wide grin on his face and his eyes shined with mischief. Dean ignored him to admire Castiel up close once more. “How’s it going, Professor?”

“Anna, how do you know this man?”  Castiel’s eyes flitted to Anna, ignoring Dean’s question.

“Brother, I’d rather not say out loud.” _Brother?_ Dean stopped breathing.

“Come on, bro. Its obvious Dean was part of Anna’s sexual revolution.” Dean was shocked at the crass statement.

“Are you courting my sister while already committed in an existing relationship?” Dean had to take a moment to translate Cas’s proper wording into something he could understand.

“I was flirting, not courting or whatever!” Dean answered the accusation. Castiel just stared at Dean, his fury rolling off of him.  “What’s wrong professor, want me to take you out on a date instead?” Dean deflected the accusation. Castiel’s fury fell off his face, shame filling it

“Yes!” The shorter man yelled. “Castiel accepts your offer for a date.” The man slapped Castiel on the back and grinned more, as if it was his plan all along. Anna blanched in response. Dean was very confused. “Friday night at 8pm, right here at this lovely establishment!”

“I’m working Friday night.” Dean answered automatically.

“Tomorrow it is. Castiel, give him your number.”

“He already has it.” Castiel answered.

“Good work, baby bro!” The shorter man pulled both Anna and Castiel away from Dean with surprising strength. Dean sat back down on his stool. In a matter of 10 seconds, he met an old lover’s brother and then was set up on a date with him tomorrow.

Ellen had stopped cleaning the glasses to watch the exchange. “That was strange.” Dean nodded in agreement. It might’ve not been his usual method of securing a date and yet, he was happy with the result. He sent a quick text to Castiel, making sure to give him an exit if necessary.

 

Dean: _You don’t have to, but I would like to take out tomorrow. Text me back with your answer._

 

Dean was driving home, staying only a few minutes longer to make sure he wouldn’t meet the family in the parking lot again. He felt his phone vibrate and waited until a red light to check. It was short.

 

Professor Castiel: _Yes._


	10. First Date

**Summary for the Chapter:**

> “You look good enough to eat,” his mouth follows with, as consolation to its earlier mistake. 
> 
> “I imagine I don’t taste very good.” Castiel answers, eyeing his shoulder.

Dean Winchester is too attractive for Castiel’s own good. Despite Dean’s lies, despite learning Dean has a girlfriend or not, despite having a previous  _ sexual _ relationship with his sister, Castiel cannot get his frustrating features out of his head. It might be bordering on an obsession, if he had the energy to devote to it. Castiel hopes by accepting the date from Dean’s text, rather than the date Gabriel rudely accepted on his behalf, that it will flush those thoughts from his mind. 

Castiel hopes that Dean chews his food with his mouth open. That he openly lies about his profession again and everything else. He hopes Dean is rude to the waitstaff. He hopes he mentions any and all exes in vivid details. Castiel hopes he talks too much. Castiel hopes this first date is a disaster, so he has a reason to reject Dean and get him out of his life permanently. Castiel hopes Dean is a terrible kisser, but he has no intention on finding out. He has been an unwelcome distraction and it needs to stop. He paid much too close attention to his brother Sam in the past semester. Sam is a diligent student with unoriginal ideas.

Now, Castiel is hiding in the bathroom, the door locked and latched, to keep Gabriel out. It was one of the few features he had added, the first time Gabriel came to visit. The extractor fan is running, the buzzing lulling Castiel as he looks in the mirror. He can’t decide whether he wants to shave or not. His indecision is marred by wanting to look good for Dean and not wanting to look for Dean. His stubble is bothersome, so Castiel grabs a razor. 

He finishes quickly, leaving only a couple of nicks on his neck, he wipes down with a towel. He gazes into his eyes in the mirror. It’s only a date. He takes a last breath in his solitude and unlocks the bathroom door. Gabriel is waiting just outside, his arms crossed, wearing a frown. “How could you let a locked door come between us, baby bro?”

“For my own safety.” Castiel answers, walking to his closet to get dressed. 

“I’m offended you would think I would endanger you before your big date with Dean-o.” Gabriel throws himself on the bed. 

Castiel glances at the clock, contemplating on getting ready early to avoid being late or being purposefully late to annoy Dean. This is the reason why Castiel hates dating so much. So much posterity, indecision, and wasted energy. Castiel arrives at his closet to find most of his clothes missing. “Gabriel...” The accusation clear without anymore words. He finds only a dark black pair of jeans and a long sleeve button down shirt. 

“I know what looks good on you.” Gabriel doesn’t get up from the bed. 

“That’s disturbing.” Castiel grabs the jeans and pulls them on. It’s not worth the argument, when he could be late or early. He can decide later. His shirt is buttoned up, Castiel reaches for a tie. 

“I’m observant.”

“Where are my ties?” Castiel lurches over Gabriel on his bed. He pulls on the comforter to pull Gabriel down.

“I hid them.” He answered honestly.

“Anna!” Castiel shouts, the small house making his deep voice carry to all corners. 

Anna walks into the bedroom, a blue tie in her hand, already tied and lays it over Castiel’s head. She says nothing. She just sits on Castiel’s bed with Gabriel, watching Castiel finish tying his tie. “You look handsome.” She finally admits. 

“Think Dean-o will appreciate it?” 

“I don’t know, Gabriel.” Anna gets up to walk out of the room. 

“Get out of my bedroom.” Castiel commands as he pulls on his dress shoes. He pulls closed the door and locks it with a key. Gabriel cannot be trusted. Castiel leaves his house thirty minutes early and arrives at the Roadhouse with fifteen minutes to spare. He hides in his car and takes a deep breath. After five minutes, Castiel decides he has waited long enough and enters the restaurant. He sees the young waitress who was in charge of the trivia the previous night. She smiles at him brightly and directs him to a booth where he finds Dean Winchester already waiting for him.

~~~~

Dean Winchester wants to make a good impression. He made his best effort. He showered twice to get the grease out of his hair because the oil pan fell on his head today. It was his own fault for being distracted. Dean shaved and even attempted to iron his red button down shirt. He wore a black undershirt and his favorite red shirt, unbuttoned. He wore his cleanest pair of jeans, the ones that weren’t covered in bacon grease or oil. Dean made all this effort because he was nervous. Professor Castiel Novak had agreed to a date with him and it made Dean nervous. He kept his phone with him, just waiting for a text message from Castiel calling the date off.

He knew the professor was far from his league, a phd candidate that was smarter than Sammy couldn’t possibly be interested in him, could he? Dean resolved himself to tell Castiel the truth about him being a teacher, he likely figured it out already. It was a fun fantasy while it lasted. Dean wanted the date to go well. Dean gets to the roadhouse early, about thirty minutes early. Jo sits him down in a booth and laughs when he mentions Castiel will be here at the top of the hour. She brings him a soda and walks away laughing again. Dean is nervous, so he drinks the whole glass immediately. He regrets that decision ten minutes in, because he has to use the restroom. He doesn’t want to leave the table, but he doesn’t want to fight his bladder the entire date. He gives up and runs to the bathroom. 

He leaves the men’s room just in time to see Castiel at the door, talking to Jo. He scurrys to the table to calmly sit down. He puts on his best smile and watches Castiel walk behind Jo to the table. He’s dressed in black jeans, not hsi slacks. He still has a long sleeve button and he’s wearing a tie again. Dean really loves the tie. His smile grow bigger as Castiel sits down across the table from him. 

The first thing wants to say is how handsome the professor looks. He says the words in his head, carefully to make sure he doesn’t screw it up. He opens his mouth, “I’m not a teacher!” blurts out his mouth. Castiel looks mildly shocked at the revelation. “You look good enough to eat,” his mouth follows with, as consolation to its earlier mistake. 

“I imagine I don’t taste very good.” Castiel answers, eyeing his shoulder. 

Dean smirks. “We’ll just have to see how this date goes to find out.” Those words cause Castiel to blush bright red. He coughs and looks away from Dean. Jo arrives to take Castiel’s drink order. He orders a beer and a bacon double cheeseburger with fries. Dean orders the same and looks at Castiel with admiration. 

“I’m unaccustomed to this sort of attention.” Castiel admits. He stares right back at Dean. Dean smiles grows as they continue to stare at other. 

“Generally, people get to know each other on a date.

Castiel nods. “You are not a teacher?” Dean shakes his head and appears ashamed. “What is your occupation?”

Though his wording was strange, Dean answered. “I’m a mechanic at Bobby’s Auto Shop, down by the salvage yard.” 

“Oh.” Was all Castiel said. “Why did you lie to me about your job?”

Dean sighed and wished he could take it back. “I wanted to impress you.”

“Oh.” Dean and Castiel sat in silence for five minutes as they both thought about how to continue the conversation. “When I was forced into speed dating, I was told to ask rapid fire questions within the timeframe to make the most of the limited time. Should we try that?” 

“Um, okay.” Dean thinks it a bit odd. 

“Favorite food?” Castiel started.

“Pie.” Dean smiles.

“Cheeseburgers.” Castiel responds, he gestures to Dean to continue.

“Family?” 

“Yes, I have several brothers and sisters.” Dean waits for him to elaborate or name them. 

“Sammy is my only brother, younger by four years.” Castiel nods. 

“Favorite author?”

“Vonnegut.” Dean states proudly.

“Miguel de Cervantes.”

“Don Quixote?” Castiel nods. 

“Preferred music?” Castiel continues. 

“Rock classics.” Dean’s arms explode outwards. 

“Classical.” Dean rolls his eyes a bit but his smile didn’t falter. 

“Favorite television show?”

“I don’t own a television.”

“Dude, seriously? I love watching Dr. Sexy M.D.”

The questions were interrupted by the arrival of their food. Castiel quickly takes a bite of his cheeseburger, his face full of joy. “These make me very happy.” He comments as he watches Dean take a bite out of his own burger. 

Dean watches carefully and thinks:  _ Wow.  _


	11. Pie

**Summary for the Chapter:**

> Dean meets someone unexpected and it breaks Castiel's patience.

 

Castiel is screwed. At each opportunity, Dean becomes more than Castiel had originally thought. He hate himself for thinking that Dean might be a broken and burnt shell of a man. It would be easier if he was. He could break off this relationship before it began, even if he could barely resist the temptation to agree to this date.

Despite the rocky beginning, Castiel enjoyed himself and the food. Dean had ordered a slice of pie for dessert with two forks. Jo approached the table with a box. She set the box down. “Sir, thank you for joining us.” She smiled at Castiel, then frowned at his date.  “Dean, don’t be late for your shift tomorrow.”

“Yeah, yeah.” Dean said taking the pie, not questioning the box. “Coffee and pie at my place?” 

 

~~~~

The data was going great! Dean didn’t make an ass out of himself and he really hoped the date continued with coffee at his place. Castiel didn’t respond to the offer of coffee and pie, so Dean waited. As they started walking to the door, Dean noticed a familiar brunette in a booth, he turned away, to avoid eye contact. Meeting an ex during a date was not ideal. He kept his gaze away and barely noticed the small child colliding into his legs. 

“Ooof, hey,” Dean said, lifting the small boy to his feet with one arm, “you alright buddy?” The kid looked up and nodded then ran away towards Lisa. Uh oh.

“Dean?” Lisa asked, her eyes flitting around nervously as well. “How are you?”

“Hi, Lisa. I’m great!” 

“Good, good.” Lisa muttered looking around. 

“Is that Ben?” Lisa nodded, not looking at him still, holding on to Ben. “Cute kid.” 

“Lisa, who are you talking to?” A burly man in a leather jacket asked coming from behind Castiel and Dean. 

“Just saying hi to a friend, he was just leaving.” Dean looked to the man and down to Ben and saw the same shade of hair and same eyes. It must be Ben’s father. 

“Get away from her, man.” He threatened.

“Excuse us, we’re just finishing our date.” Castiel suddenly spoke up from next to Dean. Ben’s father looked a little shocked and embarrassed, nodding as Castiel pulled Dean towards the exit. Dean let Castiel pull him away, wondering what the hell had just happened. 

Once out the door, Castiel withdrew his grasp and looked at Dean squarely in the face. “You have a son?!” Dean said nothing, too shocked to respond. “Is there anything else you are lying about?”

“What? No! Ben is not my son!” Dean shouted back at Castiel. “I’m not lying!”

“I don’t trust your current ability to tell me any sort of truth.”

“Ask me anything, right now, I’ll tell the truth. You can call Sammy to confirm.”

“Where are your parents?”

Dean sighed. It was never a good topic for a first date. “My mother died when I was a kid in a house fire.” He said in a flat practiced voice. “I ran away from my old man when I was sixteen and took Sammy with me. I don’t care if he’s alive or not, he wasn’t much of a father.” Dean shoved the pie in Castiel’s arms. “I’m done trying to impress you or prove I’m telling the truth. Have a nice life, Castiel.” Dean walked away before he finished his last words. He climbed into his black muscle car and drove away from the Roadhouse, leaving Castiel with a pie and a glimpse into the shit that his life is. 


	12. Six Months Later

**Summary for the Chapter:**

> Castiel is late to his night class. He blames the rain.

**Six Months Later**

 

Castiel is late for night class. His shoes are soaked from a random rainshower in June. He didn’t think to bring an umbrella, it was already summer. He was lucky he carried his trenchcoat no matter the weather. His messenger bag is filled with freshly copied syllabuses for his Intro to Philosophy class. A requirement of professors who lack the tenure to decline. It was a blessing in disguise, with more classes to teach over the spring and summer semesters, Castiel had less time to dwell on any personal matters of his own.

During the spring semester, he left his domicile early in the morning to have his early morning run and he spends at least 12 hours at the university teaching classes, grading papers, having office hours and volunteering at any event that would take him. He no longer saw Sam Winchester in his class, although he did notice the taller brother walking with a short blonde across campus occasionally. Castiel just ignored their presence and nodded when the blonde shouted hello. 

As summer semester began, his classes dwindled to more night classes filled with unconventional students. It was refreshing to deal with adults who want to learn, although he would have have more time for questions. Studying after a few years out of school can be challenging to relearn. Castiel ran in the hallway, his shoes squishing on the floor, his trenchcoat flying behind him. He didn’t know the room number, so Castiel guessed as he opened a door. He interrupted a night time history class being taught by Balthazar. 

Balthazar gave him a look of confusion that also said, ‘Find your own classroom.’ Castiel closed the door, chastising himself as he checked his planner for the correct room. It was right across the hall from Balthazar’s class. Castiel checked his appearance as best he could and straightened his coat. He walked through the door and noticed all of his students were quietly talking in their seats. 

“Evening, class. I am sorry for my lateness, the rain caught me by surprise.” He set down his messenger bag and took off his coat. He also took off his shoes, watching as his students stared in awe. “This is introduction to Philosophy, if you were looking for American History, its right across the hall. I am Professor Novak. Welcome.”

Castiel surveyed his class, a mix of younger and older students stared at him. The room was quiet. In the far back of the room, a familiar face gaped at him. It was the sharp handsome face of Dean Winchester. What was he doing in his night class?

**Author's Note:**

> First Supernatural Fic!
> 
> 12/26/17  
> -Guera-


End file.
